I like the ideas being thrown around. I’m sure there must be people out there who would do the hike but aren’t prepared to actually provide equipment for the flag raising. Having a “veteran-led group” notion allows a person to sign up for a peak and ensure that it is covered, and then open it up for others to join in on that summit to support it, but who don’t have to worry about how to build a flagpole, etc.
In fact, I think some wording with the signups might be helpful to emphasize that the signups are the guarantee of at least a hiker & flag, but that others are welcome to join, anywhere from sharing the hike to just arriving separately on the summit.
A planning party is a wicked good idea.